The hard part is one of the selling points to a seller to do a lease purchase is no realtor fees.  

That way, they have first hand knowledge of what needs to be done to properly manage their investments before putting it in the hands of a third party.

The HOA part is definitely what makes it or breaks it depending on cost, services provided, and bylaws.

Should there be paperwork signed by both parties (seller and buyer) stating all of the issues if that is the case?

Software/Programs used in Real Estate – What have you found as the most useful software/programs in real estate analysis or is a third party typical involved to conduct feasibility studies or Argus Runs? 

And they might have to to so anyway in order to avoid a charge from the irs of basis shifting in a 1031 exchange with a related party. 

Chatting on the phone can go a long way to making sure you a quality guest.We are pretty far out of town down the lake so we don't get too many party type requests which is good for us!

Typically buying a condo will result in having non-student neighbors too, so make sure he is aware of that and does not throw massive parties all the time

There are lots of opportunities and I am sure you will find something that works out for you and the other party.

I’m looking to setup a billing system for the tenants or use a 3rd party service.